Mujqcmtvyhjoly-ctdwivfpsa- | 185610-61-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Mujqcmtvyhjoly-ctdwivfpsa-
• 英文别名: [(2R,3R,4R,5R)-5-[2-acetamido-6-(diphenylcarbamoyloxy)purin-7-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 185610-61-1
• 化学式: C₃₁H₃₀N₆O₁₀
• 分子量: 646.613
• InChiKey: MUJQCMTVYHJOLY-CTDWIVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Mujqcmtvyhjoly-ctdwivfpsa- 、 四乙酰核糖 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-(diphenylcarbamoyl)guanine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹

  摘要：

  Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin-(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethane-sulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-beta-D-ribofuranosyl isomer was shown to be both the kinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.

  DOI：

  10.1021/jo9617023
• 作为产物：
  描述：

  四乙酰核糖 在 苯磺酰胺 、 四氯化锡 、 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 1.5h， 生成 Mujqcmtvyhjoly-ctdwivfpsa-
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹

  摘要：

  Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin-(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethane-sulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-beta-D-ribofuranosyl isomer was shown to be both the kinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.

  DOI：

  10.1021/jo9617023